Citation: Yu Youpei, Duan Wengui, Lin Guishan, Kang Guoqiang, Wang Xiaoyu, Lei Fuhou. Synthesis, Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of Novel 4-Methyl-1, 2, 4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1647-1657. doi: 10.6023/cjoc201912042 shu

Synthesis, Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of Novel 4-Methyl-1, 2, 4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring

a.
College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
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Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University for Nationalities, Nanning 530008

Corresponding author: Duan Wengui, wgduan@gxu.edu.cn
Received Date: 28 December 2019
Revised Date: 27 February 2020
Available Online: 11 March 2020
Fund Project: the Specific Research Project of Guangxi for Research Bases and Talents AD18126005Project supported by the National Natural Science Foundation of China (No. 31870556) and the Specific Research Project of Guangxi for Research Bases and Talents (No. AD18126005)the National Natural Science Foundation of China 31870556

Figures(6)

A series of novel 4-methyl-1, 2, 4-triazole-thioethers containing gem-dimethylcyclopropane ring were designed and synthesized by multi-step reactions in search of potent novel bioactive molecules. Structures of all the target compounds were characterized by means of UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As indicated in bioassay results, 2 compounds exhibited excellent antifungal activity against Physalospora piricola, which are much better than that of the commercial fungicide of chlorothalonil used as positive control. Also, at 100 μg/mL, 4 compounds displayed prominent herbicidal activity against the root-growth of rape (Brassica campestris), which are much better than that of the commercial herbicide of flumioxazin used as positive control. In the interest of developing more effective antifungal compounds against P. piricola, the preliminary analysis of three-dimen-sional quantitative structure-activity relationship (3D-QSAR) was carried out using the molecular field analysis (CoMFA) method, and a reasonable and effective 3D-QSAR model (r²=0.985, q²=0.509) has been established.
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